Aryloxyethylene amine compounds are known as useful intermediates and find application in pharmaceuticals and pesticides, among other uses. For example, U.S. Pat. No. 2,133,779 discloses such compounds are useful as antioxidants in vulcanized rubber compounds. U.S. Pat. Nos. 4,792,570; 4,536,503; and 4,792,551 disclose that certain biphenyloxyaminoalkanes, naphthoxyalkylamines, and 9-anthryloxyaminoalkanes have anti-inflammatory and analgesic activity; typically these compounds are prepared through an aryloxyalkylhalide intermediate. U.S. Pat. No. 7,081,465 discloses certain naphthyloxyaminoalkyane compounds for use as antihyperglycemic agents prepared by reacting naphthol with a dihaloalkane in the presence of a base to form a naphthoxyalkylene halide intermediate which is further reacted with an amine in the presence of an acid binding agent.
U.S. Pat. No. 5,030,755 discloses a method of preparing a phenoxyethylamine by reducing a substituted phenoxyacetaldehyde oxime with hydrogen in the presence of a Raney-nickel catalyst.
German Patent Publication DE 19711004 A1 discloses the use of 2-oxazolidinone to prepare phenoxyaminoalkanes from low molecular weight phenols; namely, 2-4-(Phenoxyphenoxy) ethylamine and ethyl 2-(phenoxyphenoxy)ethylcarbamate are sequentially prepared in high yield and selectivity by the aminoethylation of 4-phenoxyphenol with 2-oxazolidinone under inert atmosphere, followed by amidation of 2-4(phenoxyphenoxy)ethylamine with carbonate derivatives.
Japanese Patent Publication No. JP 2592732 B2 discloses a method of producing phenoxyethylamines by reacting, under base conditions, low molecular weight phenols and 2-oxazolidinone. It states that phenoxyethylamines are important raw materials for pharmaceuticals and pesticides.
U.S. Pat. Nos. 6,384,280 and 6,649,800 teach the use of 2-oxazolidinone or a derivative thereof in aminoethylation transformations involving high molecular weight polyalkylphenols to provide polyalkylphenoxyaminoalkanes of the type disclosed in U.S. Pat. Nos. 5,669,939 and 5,851,242. A process for preparing the 2-oxazolidinone in-situ for aminoethylation of polyalkylphenols to polyalkyphenoxyaminoalkanes is disclosed in U.S. Pat. No. 6,486,352. Their use as an intermediate in the preparation of fuel additives has been described in U.S. Pat. No. 6,114,542 in the preparation of polyalkyl or polyalkenyl N-hydroxyalkyl succinimides from various aryloxyalkene amines and polylakyl or polyalkenyl succinic anhydrides was disclosed, along with their use in fuel compositions.
The processes above typically have poor yields and/or employ undesirable reactants or by-products in the reaction mixture which require further separation. The modified process of the present invention enables one to achieve exceptionally high conversion of an aromatic hydroxyl compound—starting material, into the desired aryloxyalkylene amine products. This process also eliminates the need to dispose of large quantities of unwanted by-products. The process is readily amenable to manufacturing and incurs a minimal cost increase over the previously reported methods.